Pyridine → HCID 21493324, compound

HRID 1973230Notes

Reaction equation

HRID 1973230 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.N1C=CC=CC=1.[Cl:17][CH2:18][C:19](Cl)=[O:20]>CCOCC>[CH3:9][O:8][C:7]1[C:2]([NH:1][C:19](=[O:20])[CH2:18][Cl:17])=[N:3][CH:4]=[C:5]([Br:10])[CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chloride2×HCID 222714075-Bromo-3-methoxypyridin-2-amine

Product 1

HCID 21493324HCID 21493324, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-amino-3-methoxy-5-bromopyridine (20.3 grams) in absolute ether (200 ml) is charged into a glass reaction vessel equipped with mechanical stirrer and addition funnel. The solution is cooled to a temperature of about 5° C and pyridine (20 ml) is added thereto. A solution of chloroacetyl chloride (11.3 grams) in ether (50 ml) is then slowly added, with stirring, to the flask over a period of about 30 minutes resulting in the formation of a precipitate. The temperature of the reaction mixture is kept below about 10° C during the addition of the chloroacetyl chloride and stirring is continued thereafter for a period of about 1 hour to ensure the completion of the reaction. The precipitate which has formed is then recovered by filtration and is washed first with aqueous potassium carbonate and then with water. The washed product is then dried in a vacuum desiccator to yield the desired product N-(3-methoxy-5-bromo-2-pyridyl)-α-chloroacetamide.

Workup

  1. customequipped with mechanical stirrer and addition funnel
  2. additionis added
  3. customresulting in the formation of a precipitate
  4. stirringstirring
  5. waitfor a period of about 1 hour to ensure
  6. customthe completion of the reaction
  7. customThe precipitate which has formed
  8. filtrationis then recovered by filtration
  9. washis washed first with aqueous potassium carbonate
  10. customThe washed product is then dried in a vacuum desiccator

Sources & evidence

ORD record
ord-5ac823ac449d44189a0cf09223d6ee4d
Source dataset
uspto-grants-1976_12
Patent number
US03996352

Reaction notes

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